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Chem261
MODULE 1: The Basics: Bonding and Molecular Structure
The Structural Theory of Organic Chemistry
- isomers: the important of structural formulas
- the tetrahedral shape of methane
ionic bonds
- covalent bonds
Writing Lewis Structures
Exceptions to the Octet Rule
Formal Charge
Summary of Formal Charges
Resonance
Summary of Rules for Resonance
Quantum Mechanics
Atomic Orbitals and Electron Configuration
Molecular Orbitals
The Structure Of Methane And Ethane: sp3 Hybridization
The structure of Methane
The Structure of Ethane
The Structure of Ethene (Ethylene): sp2 Hybridization
Restricted Rotation and the Double Bond
Cis-Trans Isomerism
The Structure of Ethyne (Acetylene): Sp Hybridization
Bond Lengths of Ethylene, Ethene, and Ethane
A Summary of Important Concepts that Come From Quantum Mechanics
Molecular Geometry: The Valence Shell Electron Pair Repulsion Model
- methane
- ammonia
- water
- boron trifluoride
- beryllium hydride
- carbon dioxide
How to interpret and Write Structural Formulas for cyclic and acyclic molecules
- dash structural formulas
- condensed structural formulas
- bond-line formulas
- three-dimensional formulas
Text Sections: 1.2-1.17
Chapter1 Homework: 1.3, 1.5, 1.6, 1.7, 1.8, 1.9, 1.10, 1.11, 1.13, 1.14, 1.15, 1.16, 1.17, 1.18, 1.19, 1.20,1.
21, 1.22, 1.23, 1.24, 1.25, 1.27, 1.28, 1.29, 1.30, 1.31, 1.32, 1.33, 1.34, 1.35,
1.36, 1.37, 1.38, 1.39, 1.40, 1.41, 1.42, 1.43, 1.44, 1.45, 150
MODULE 2:Families of Carbon Compounds: Functional Groups, Intermolecular Forces, and
Infrared (IR) Spectroscopy
Hydrocarbons
- alkanes
- alkenes
- alkynes
- benzene: A representative Aromatic hydrocarbon
Polar Covalent Bonds
Polar and Nonpolar Molecules
Dipole Moments in Alkenes
Functional Groups
- alkyl groups and the symbol R
- phenyl and benzyl groups
2
- alkyl halides or haloalkanes
- alcohols
- ethers
- amines
- aldehydes and ketones
- carboxylic acids
esters
amides
- nitriles
Summary of Important Families of Organic Compounds
Physical Properties and Molecular Structures
- ion-ion forces
- dipole –dipole forces
- hydrogen bonds
- van der walls forces
- solubilities
- guidelines for water solubility
Infrared Spectroscopy: An Instrumental Method for Detecting Functional groups
- hydrocarbons
- alcohols and phenols
- carboxylic acids and esters
- aldehydes, ketones
- amines
- amides
- nitriles
How to gain Structural Information from Molecular Formulas and the Index of Hydrogen Deficiency
Text Sections: 2.1-2.17, 4.17
Chapter 2 Homework: 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2. 9, 2.10, 2.12, 2.13, 2.16, 2.17, 2.18, 2.19, 2.20,
2.21, 2.22, 2.23, 2.24, 2.25, 2.26, 2.27, 2.28, 2.29, 2.30, 2.31, 2.32, 2.33, 2.34, 2.35,
2.36, 2.37, 2.38, 2.39, 2.40, 2.41, 2.42, 2.45, 2.46, 2.47, 2.48, 2.49, 2.50, 2.51, 2.52, 2.53, 2.54, 2.55, 2.56,
2.57
MODULE 3: An Introduction to Organic Reactions: Acids and Bases
Reactions and their Mechanisms
Homolysis and Heterolysis of Covalent Bonds
Acid-Base Reactions
- the Bronsted-Lowry Defination of acids and Bases
- the lewis Definition of Acids and Bases
- opposite charge attract
Heterolysis of Bonds to Carbon: Carbocations and Carbanions
Electrophiles and Nucleophiles
The Use of Curved Arrows in Illustrating Reactions
The strength of Acids and Bases: ka and pka
The acidity Constant, ka
Acidity and pka
Predicting the Strength of Bases
How to Predict the Outcome of Acid-Base Reactions
Water Solubility as the Result of Salt Formation
The Relationships between Structure and Acidity
- the effect of hybridization
- inductive effects
The Acidity of Carboxylic Acids
- an explanation based on resonance effects
- an explanation based on inductive effects
- inductive effects of other groups
- the effect of solvent on acidity
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Organic Compounds as Bases
A Mechanism for an Organic Reaction
Acids and Bases in Nonaqueous Solutions
Acids – Bases Reactions and the Synthesis of Deuterium and tritium-Labeled Compounds
Text Sections: 3.1-3.8, 3.11-3.16.
Chapter3 Homework: 3.1, 3.2, 3.3, 3.5, 3.7, 3.8, 3.9, 3.10, 3.14, 3.15, 3.16,3.18, 3.18, 3.20, 3.21, 3.22,
3.23, 3.24, 3.25, 3.26, 3.27, 3.29, 3.31, 3.32, 3.33, 3.34, 3.35,3.37, 3.43, 3.44
MODULE4: Nomenclature and Conformations of Alkanes and Cycoalkanes
Introduction to alkanes and Cycloalkane
Shape of Alkanes
IUPAC Nomenclature of Alkanes, Alkyl Halide, and Alcohols
- nomenclature of unbranched alkyl groups
- nomenclature of branched-chain alkanes
- nomenclature of branched alkyl groups
- classification of hydrogen atoms
- nomenclature of alkyl halides
- nomenclature of alcohols
Nomenclature of Cycloalkanes
- monocyclic compounds
- bicyclic compounds
Nomenclature of Alkenes and Cycloalkenes
Nomenclature of Alkynes
Physical Properties of Alkanes and Cycloalkanes
Sigma Bonds and Bond Rotation
Newman Projections and How to Draw Them
How to do Conformational Analysis
Conformational Analysis of Butane
Stereoisomers and Conformational Stereoisomers
The relative Stabilities of Cycloalkanes: Ring Strain
-cyclopropane
-cycobutane
-cyclopentane
Conformations of Cyclohexane: The chair and the boat
Conformations of Higher Cycloalkanes
Substituted Cyclohexanes: Axial and Equatorial Hydrogen Groups
How to Draw Chair Conformational Structures
A Conformational Analysis of Methylcyclohexane
1,3-Diaxial interactions of a tert-Butyl Group
Disubstituted Cycloalkanes: Cis – trans Isomerism
Cis – Trans isomerism and Conformational Structures of Cyclohexanes
Bicyclic and Polycyclic Alkanes
Chemical Reactions of Alkanes
Synthesis of Alkanes and Cycloalkanes
Hydrogenation of alkenes and alkynes
How to Gain Structural Information from Molecular Formulas and the Index of Hydrogen Deficiency
Text Sections: 4.1-4.17.
Chapter 4 Home work: 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8, 4.9, 4.10, 4.11, 4.12, 4.15, 4.16, 4.17, 4.18,
4.19, 4.20, 4.21, 4.23, 4.24, 4.25, 4.26, 4.27, 4.28, 4.29, 4.31, 4.32, 4.33, 4.34, 4.35, 4.36,
4.37, 4.39, 4.40, 4.41, 4.42, 4.43, 4.45, 4.48
MODULE5: Stereochemistry: Chiral Molecules
Isomerism: Constitutional Isomers and Stereoisomers
Enantiomers and Chiral Molecules
A Single Chirality Center Causes a Molecule to be Chiral
How to test for Chirality: Planes of symmetry
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Naming Enantiomers: The R, S –System
How to Assign (R) and (S) Configurations
Properties of Enantiomers: Optical Activity
- specific rotation
Plane polarized light
The polarimeter
The Origin of optical Activity
Racemic forms
Racemic forms and Enantiomeric Excess
The Synthesis of Chiral Molecules
- racemic forms
Moclecules with More than One Chirality Center
- meso compounds
How to name Compounds with more than one Chirality Center
Fischer Projection Formulas
How to Draw and Use Fischer Projections
Stereoisomerism of Cyclic Compounds
Cyclohexane Derivatives
Relating Configurations through Reactions in which No Bonds to the Stereogenic Carbon are broken
Relative and Absolute Configurations
Separation of Enantiomers: Resolution
- Pasteur’s method for separating enantiomers
- Current method for resolution of enantiomers
Compounds with Stereogenic Center other than Carbon
Text Sections: 5.1- 5.4, 5.6-5.10, 5-12 –5-17.
Chapter 5 Homework: 5.2, 5.4, 5.5, 5.6, 5.8, 5.9, 5.10, 5.11, 5.12, 5.13, 5.14, 5.16, 5.17, 5.18, 5.19, 5.20,
5.21, 5.22, 5.23, 5.24, 5.25, 5.26, 5.27, 5.285.33, 5.34, 5.35, 5.36, 5.37, 5.38,
5.39(not q), 55.41, 5.42, 5.44, 5.45, 5.46
MODULE 6.Ionic Reactions: Nucleophilic Substitution and Elimination Reactions of Alkyl Halides
Organic Halides
Physical Properties of Organic Halides
Nucleophilic Substitution Reactions
- nucleophiles
- leaving groups
Kinetic of a nucleophilic substitution reaction: An SN2 Reaction
How do we measure the rate of this reaction?
What is the order of this reaction?
A Mechanism for the SN2 Reaction
Transition State Theory: Free – Energy Diagrams
The Stereochemistry of SN2 Reactions
The Reaction of tert-Butyl chloride with hydroxide Ion: An SN1 Reaction
Multistep Reactions and the Rate-Determining Step
A Mechanism for the SN1 Reaction
Carbocations
- the structure of carbocations
- the relative stabilities of carbocations
The Stereochemistry of SN1 Reactions
- reactions that involved Racemization, solvolysis
Factors Affecting the Rates of SN1 and SN2 Reactions
- the effect of the structure of the substrate
- the effect of the concentration and strength of the nucleophile
- solvent effects on SN2 reactions: Polar protic and aprotic solvents
- solvent effects on SN1 reactions: The ionizing ability of the solvent
- the nature of leaving group
- the unreactivity of vinylic and phenyl halides
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- The Hammond-Leffler Postulate
Summary: SN1 versus SN2
Organic Synthesis: Functional Group Transformations Using SN2 Reactions
Elimination Reactions of Alkyl Halides
- dehydrohalogenation
- bases used in dehydrohalogenation
- mechanism of dehydrohalogenations
The E2 Reaction
The E1 Reaction
How to determine Whether Substitution or Elimination is Favored
- SN2 versus E2
- tertiary halide: SN1 versus E1
- overall summary
Text Sections: 6.1- 6.6, 6.8-6-19.
Chapter 6 Homework: 6.1, 6.26.3, 6.5,6.6, 6.7, 6.8, 6.9, 6.10, 6.12, 6.136.14, 6.15, 6.16, 6.18, 6.19 (a, b,
only) ,6.20, 6.21, 6.22, 6.23, 6.26, 6.27, 6.29, 6.30, 6.31, 6.33, 6.34, 6.37, 6.38,
6.41, 6.46, 6.47.
MODULE7. Alkenes and Alkynes: Properties and Synthesis,
Elimination Reactions of Alkyl Halides
Introduction
The (E) – (Z) System for Designating Alkene Diastereomers
Relative Stabilities of Alkenes
- heat of reaction
- overall relative stabilities of alkenes
Cycloalkenes
Synthesis of Alkenes via Elimination Reactions
Dehydrohalogenation of Alkyl Halides
How to Favor an E2 Mechanism
- Zaitsev’s rule: Formation of the most substituted alkene is favored with a small base
- formation of the least substituted alkene using a bulky base
- the stereochemistry of E2 reactions: The orientation of group in the transition state
- E2 Elimination where there are two axial cyclohexane hydrogen atoms
- E2 Elimination where the only eligible axial cyclohexane hydrogen is from a less
stable conformer
Acid-Catalyzed Dehydration of Alcohols
- mechanism for dehydration of secondary and tertiary alcohols: An E1 reaction
- carbocation stability and the transition state
- acid-Catalyzed Dehydration of Secondary Alcohols: An E1 Reaction
Carbocation Stability and the Occurrence of Molecular Rearrangements
- rearrangements during dehydration of secondary alcohol
The Acidity of Terminal Alkynes
Synthesis of Alkynes by Elimination Reactions
Mechanism of Dehydrohalogenation of Vicinal Dibromide to form Alkynes
Substitution of the Acetylenic Hydrogen Atom of Terminal Alkynes
Alkylation of Alkynide Anions
Hydrogenation of Alkenes and Alkynes
An introduction to organic Synthesis,
Text Sections: 7.1- 7-16.
Chapter 7 Homework: 7.1, 7.2, 7.3, 7.4, 7.6, 7.7, 7.8, 7.9, 7.10,7. 11, 7.12, 7.13, 7.14, 7.15, 7.17, 7.19(b,
c, d), 7.20, 7.21, 7.22, 7.26, 7.27, 7.28, 7.29, 7.33, 7.34(a, b) 7.36, 7.37,
7.38, 7.7.39, 7.40, 7.41, 7.43, 7.44, 7.46, 7.47, 7.48, 7.52, 7.54
T.W.Graham Solomons and Craig B. Fryhle, Organic Chemistry, 10th edition